Tanner re-lives the first large enterprise deal he landed for his startup. When selling in a company's early stages, it truly takes a village to get an enterprise deal across the line. You have no SOPs, legal red-lining & security protocols. Just a strong team, 100% focus, & a vision. That's how Tanner brought this one home. Listen to the full story! Featuring neighbor referrals, SAP, & the Jamaican legal system Tanner's Sales Tips Invest in relationships over everything You can never be 'over-threaded' in a deal Confidence goes a long way. Especially as a startup Tanner Lacey: https://www.linkedin.com/in/tanner-lacey/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Jeanna walks us through a true sales albatross: closing the biggest deal in his company's history in their fastest sales cycle ever. If closing a massive deal in 2 weeks sounds insane, that's because it is. But that is exactly what happened to Jeanna & changed the course of his selling career. Listen how! Featuring gamification, Charles Barkley, & multiple languages Jeanna's Sales Tips Relationship building is everything in sales Opt to be genuine over a people pleaser Be like a goldfish. Lost a deal? Move to the next one Jeanna Humble: https://www.linkedin.com/in/jeanna-lifungula-humble-a25b00106/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Morgan heads back to her non-profit roots in this one. Selling into an Austrialian-based non-profit & working through several firsts. Her first international deal & totally outside her typical ICP. But in any down market, you have to be flexible as a seller & take chances on any lead. Morgan did exactly that. Paid off big time! Featuring selling in a down market, international intrigue, & a pitbull rescue Morgan's Sales Tips Consider all potential impacts & outcomes blocking a deal Dip into past experiences to find new opportunities Stay up to date on every past deal. Prioritize look-alikes Morgan Buchanan: https://www.linkedin.com/in/morganbuchanan1/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Chris is the adventurous tech sales guy. In between climbing mountains, he's closing enterprise deals. He re-lives a wild deal involving one of the largest restaurant groups in the United States. He took the risk of flying out to a conference to 'run' into the prospect CEO 7 open the dialogue. Leading to a chain of events that allowed him to mark it closed won. Hear how it went down! Featuring a risky trip, free food for life, & rock climbing Chris' Sales Tips Put yourself in your prospect's shoes. Would you buy? One door closes, another opens. You gotta walk through. Always be authentic. Don't need to button up to sell. Chris Horton: https://www.linkedin.com/in/christo-horton/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Laura has been transitioning as a seller from enterprise sales to growing a startup, moving from founder-led sales to rep-led sales. While so much has been in flux, one thing remains true: people buy from people they trust. In order to build that trust, Laura has become an expert in social selling. She appears everywhere her buyers live online before they even know they're ready to buy. Being there for them with education-led conversations leads them to go to Laura first when they are ready to buy. That's exactly how she closed this deal. Have a listen! Featuring proof of concept, enterprise to startup sales, & March Madness Laura's Sales Tips Care about your prospects. It's that simple. Master open ended-questions. Live where your buyers live. Laura Erdem: https://www.linkedin.com/in/lerdem/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Krysten re-lives a deal that showcased every major aspect of why enterprise deals close: executive alignment, multi-threaded & single-threaded, involving every buyer type from top to bottom. She took this deal over mid-flight from a colleague & had to grab the baton smoothly before things fell apart. Hear how she quickly caught up to speed on the details/personalities & brought the deal home. Featuring single threading, mid-deal takeover, & teachers Krysten's Sales Tips Align your executives & the buyers. Your VP should know their VP. Thread all 3 levels: user, manager, & executive Team selling is dream selling Krysten Conner: https://www.linkedin.com/in/krystenconner/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Cassandra talks through the first closed-won deal for her & her company! Sales reps typically avoid being the first to venture down the path of selling a new persona, but not Cassandra. She sourced this opportunity from a past closed-lost deal & strong partner relationships. Dive into the metaverse with us & hear how it went down! Featuring the metaverse, partner-led sales, & TikTok dogs Cassandra's Sales Tips Strive to be the expert in any field you sell into. Don't focus on other sales reps' careers. Your journey is unique.  Work like someone else wants your job. Cause they do. Cassandra Freeman: https://www.linkedin.com/in/cassandrarfreeman/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Justin reminisces on a mega-deal missed opportunity from his Salesforce.com days.  We're talking eight figures. From working with the prospect daily for a year, building a case for a $15MM digital transformation deal, & working with Marc Benioff. This deal had everything except a final signature. Learn how it all went down. Featuring digital transformation, the Amazon Death Star, & Auntie Anne's Pretzels Justin's Sales Tips Even in a team sale, the deal falls on the rep to close. Find the deal red flags as soon as possible. Win or lose, learn everything you can working a huge deal. Justin Jay Johnson: https://www.linkedin.com/in/justinjayjohnson/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Max takes us through a deal containing true champion-building efforts. Both internal & external. Internally, he built a deep connection with his Solutions Engineer. They worked this deal together better than Jordan & Pippen. Externally, Max fostered a powerful relationship with the prospect's Dev Ops team & gave them to confidence to sell it to the CEO themselves. Hear how it went down! Featuring deal progression meetings, TCO, & the Kansas City Chiefs Max's Sales Tips Be creative with outreach & interrupt patterns.  Bring an opinion to the table. They will correct you. (great!) Build a business case with your champion. Max Tierney: https://www.linkedin.com/in/max-tierney-86762010a/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Christian walks us through his first closed-won as an AE! In the midst of a company-wide persona shift, Christian worked through deep research & LinkedIn Sales Nav like a true pro. Surfacing this international deal from nothing & closing it through dedicated personalization. Hear how he did it! Featuring lawyers, Series C funding, & goin' full Super Saiyan mode Christian's Sales Tips Create avenues to solve multiple problems. Set the tempo with consistent, timely responses. Be brutally honest about your product. Christian Erba: https://www.linkedin.com/in/christian-erba-a949191ba/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Morgan re-lives her first closed-won deal ever! Transitioning from full-time teacher to full-time seller wasn't easy, but leveraging transferable skills & a killer PLG motion ended up being the difference. Providing proof of value & taking a calculated risk to create palpable urgency led to the Docusign being completed. Featuring teaching to sales, proof of value, & Argentina Morgan's Sales Tips Need urgency? Turn off the trial Lean into value selling. Speak benefits, not features Align business & technical solutions consistently Morgan Shelly: https://www.linkedin.com/in/morganshelly/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Andrés typically works inbound leads, so this particular deal stood out as a highly strategic outbound effort on his part. He leveraged multi-threaded voice memos via LinkedIn, ran a truly thorough discovery process, & delivered a personalized demo (outside of the standard one his company expects). That approach & risk landed him the signature. Hear how! Featuring product-led prospecting, voice notes, & contemplative monks Andrés' Sales Tips Leverage job changes. Top-tier buying trigger. Be patient. Allows you to be more strategic. Avoid superficial discovery. It's all about them, not you. Andrés Angulo: https://www.linkedin.com/in/andres-angulo-growth/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Jack talks through a deal he closed that equated to SaaStr's largest outbound sponsorship deal to date. Leveraging a teammates podcast, Crunchbase, & in-person meetings at SaaStr itself, Jack worked this deal with incredible precision. Even with major bumps in the road. Namely, red tape, waiting on an executive new hire, and budget concerns. Hear how he closed this one. Featuring Crunchbase, podcast prospecting, & photography Jack's Sales Tips Be relentlessly persistent in everything you do. When it comes to quota, consistency > hot/cold streaks. Adjust follow-up to market conditions & a human touch. Jack Ryan: https://www.linkedin.com/in/paralyzed-to-peaks/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Axel re-lives a prospect look-alike deal he masterfully executed. Coming off the momentum of a recently closed inbound deal, Axel didn't sit back. Leveraging LinkedIn Sales Navigator, he found a prospect who might be dealing with similar issues.  Using the social proof of the inbound competitor & the hypothesis of similar pain, he was able to get in front of the buyer immediately & close another deal in under 3 weeks. Hear how he did it. Featuring sales humor, electric vehicles, & speaking Icelandic Axel's Sales Tips Ask for the next step. If there's value, don't wait. Always run deals with authenticity. Trust builds faster. Nobody cares about features. Personalize to their workflow. Axel Zaccardo: https://www.linkedin.com/in/axel-zaccardo/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Charlotte takes us down memory lane to a deal where the juice wasn't worth the squeeze. Selling to city locations & governments is a mixed bag. While cool to with mayors & governors, the red tape can sometimes be a nightmare. Hear how she navigated the process & eventually got it inked. Featuring 100% commission, a rough cold email, & Canada Charlotte's Sales Tips Detach yourself from the outcome. Deals ≠ your self-worth. Don’t withhold the price. Let the prospect determine their value. Disqualify to qualify. Always ask: Is the juice worth the squeeze? Charlotte Lloyd: https://www.linkedin.com/in/charlottelloydsales/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Rocco re-lives a deal that began in an excellent economy & closed in a down economy. On top of that, he sold a little-known product category at the time. So education and quantifiable value were key. Hear how Rocco brought this buyer back from ghosting with a pen in hand to sign. Featuring DiSC profile, Objection vs. Situation, & Tony Robbins Rocco's Sales Tips You're hired to sell. No matter what economy we're in Keep 1 ear to the sky. Know what impacts prospects (macro) Keep 1 ear to the ground. Be mindful of your prospect's reality (micro) Rocco Davage: https://www.linkedin.com/in/roccosavage/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Neal takes us through the deal that got away. Marking our 2nd closed-lost episode. This one is just as jam-packed with tough lessons learned. Working with some of the top brands in the world, sometimes you can assume you know a prospect's problem before asking. But that can be a costly mistake. Hear how. Featuring riding the hot hand, video prospecting, & A-list celebrities Neal's Sales Tips Spend time re-living missed opportunities. Learn more that way. Listen more than you speak. Empathy wins over features often. Know where you stand competitively at all times. Neal Goyal: https://www.linkedin.com/in/nealgoyal/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Mor had to close an enterprise sale within a month or his business would close. He re-lives the buzzer-beater deal that kept his dream alive with us. Talk about pressure. Want to improve your buyer persona research? This is the episode for you. Featuring toy commercial strategy, demo win rates, & an '8 Mile' reference Mor's Sales Tips Assume every lead isn't a fit right away. Your discovery calls will thank you. Take an obnoxious amount of notes about the most minor details. Don't ask for the sale (money). But always ask for the close (next step). Mor Assouline: https://www.linkedin.com/in/morassouline/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

Scott chats through the deal that got him to his first Presidents Club trip. As a long-time individual contributor, now Sales Enablement head, a lot of his sales training & enablement approach is based on the lessons he learned in this particular deal. Featuring sales trap setting, 20/20 hindsight, & knucks with the pope Scott's Sales Tips Innoculate objections before they arise. "Here's what you're gonna say..." People buy based on experience. Keep that top of mind constantly. Setting next steps is a muscle you have to exercise consistently. Scott Knudson: https://www.linkedin.com/in/scotttheamazing/ Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/ Junior Lartey: https://www.linkedin.com/in/juniorlartey/ Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!

How I Deal has hit the big 3-0! To celebrate, we've compiled a few great clips from the previous 29 episodes.  From initial account research to the final signature, hear some of the top takeaways from full-cycle sellers each step of the way. Featuring: Ricky Pearl - Building GTM prospect lists Cam England - LinkedIn Sales Nav 101 Maggie Blume - Don't sleep on inbounds Nick Smith - Keep emails painfully short PJ Ricketson - Discovery questions = deal trajectory Patrick Kennedy - Mobilzers vs. Champions Nolan Hansen - On-site demo magic Amelia Taylor - Running deals via Slack Nate Nasralla - Negotiating with you own team Help us out! Enjoying our conversations? Consider leaving a rating & review for the show. We love connecting with our listeners & always look to improve!